Regioisomeric α-[70]fullerene-fused lactones: Synthesis, characterization and solubility difference. Issue 51 (17th December 2020)

• Record Type: Journal Article
• Authors: Li, Dan; Li, Zong-Jun; Li, Shu-Hui; Xu, Li-Jun; Gao, Xiang
• Is Part Of: Tetrahedron letters. Volume 61:Issue 51(2020)
• Publication Date: 2020-12-17
• Subjects: Fullerenes -- Isomer effect -- Lactones -- Regioselectivity -- Solubility; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152607
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Two types of regioisomeric α -[70]fullerene-fused lactones were obtained. X-ray single crystal structures were obtained for the two types of regioisomers. A significant solubility difference is shown between the two types of regioisomers. New insight into the reaction mechanism is obtained. Abstract: Two types of regioisomeric α-[70]fullerene-fused lactones were synthesized from the reaction of C70 with 2-alkylmalonates under basic conditions. The structures of the compounds were determined unambiguously by X-ray single crystal diffraction analysis, and the compounds were further characterized with HRMS, UV–vis, 1 H NMR and 13 C NMR spectroscopies. The reactions were followed by the in situ vis-NIR measurement to study the mechanism. Interestingly, a large solubility difference was shown between the two types of regioisomers.